9-Deoxy-9-methylene-PGF-p-substituted phenyl esters

ABSTRACT

The present invention relates to novel 9-deoxy-9-methylene-p-substituted phenyl esters. These compounds are useful pharmacological agents, and are useful for the same purposes as the corresponding 9-deoxy-9-methylene-PGF-type acids.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of Ser. No. 786,250, filed Apr. 11, 1977, now U.S. Pat. No 4,098,805, issued July 4, 1978.

The present invention relates to novel 9-deoxy-9-methylene-PGF-p-substituted phenyl esters, the essential material consituting a disclosure of which is incorporated here by reference from U.S. Pat. 4,098,805. 

I claim:
 1. A prostaglandin analog of the formula ##STR1## wherein Y₁ is trans--CH═CH--, --C.tbd.C--, or --CH₂ CH₂ -- wherein M₁ is ##STR2## wherein R₅ is hydrogen or methyl; WHEREIN L₁ is ##STR3## or a mixture of ##STR4## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro;Wherein Z₁ is (1) cis--CH═CH--CH₂ --(CH₂)_(g) --CH₂ --, (2) cis--CH═CH--CH₂ --(CH₂)_(g) --CF₂ --, (3) cis--CH₂ --CH═CH--(CH₂)_(g) --CH₂ --, (4) --(ch₂)₃ --(ch₂)_(g) --CH₂ --, (5) --(ch₂)₃ --(ch₂)_(g) --CF₂ --, (6) --ch₂ --o--ch₂ --(ch₂)_(g) --CH₂ --, (7) --c.tbd.c--ch₂ --(ch₂)_(g) --CH₂ --, (8) --ch₂ --c.tbd.c--(ch₂)_(g) --CH₂ --, ##STR5## WHEREIN G IS ONE, 2 OR 3; WHEREIN R₇ is (1) --(CH₂)_(m) --CH₃, ##STR6## WHEREIN M IS ONE TO 5, INCLUSIVE, H IS ZERO OR ONE, T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, and s is zero, one, 2, or 3, the various T's being the same or different, with the proviso that not more than two T's are other than alkyl, with the further proviso that R₇ is ##STR7## wherein T and s are as defined above, only when R₃ and R₄ are hydrogen or methyl, being the same or different; andwherein L₆ is p-substituted phenoxy selected from the group consisting of ##STR8## wherein R₂₄ is methyl, phenyl, acetamidophenyl, benzamidophenyl, or --NH₂ ; R₂₅ is methyl, phenyl, --NH₂, or methoxy; and R₂₆ is hydrogen or acetamido.
 2. A prostaglandin analog according to claim 1, wherein Y₁ is --CH₂ CH₂ --.
 3. 9-Deoxy-9-methylene-16,16-dimethyl-13,14-dihydro-PGF₂, p-acetamidophenyl ester, a prostaglandin analog according to claim
 2. 4. 9-Deoxy-9-methylene-16,16-dimethyl-13,14-dihydro-PGF₂, p-benzaldehyde semicarbazone ester, a prostaglandin analog according to claim
 2. 5. A prostaglandin analog according to claim 1, wherein Y₁ is trans--CH═CH--.
 6. A prostaglandin analog according to claim 5, wherein M₁ is ##STR9##
 7. 9-Deoxy-9-methylene-16-methyl-15-epi-PGF₂, p-benzamidophenyl ester, a prostaglandin analog according to claim
 6. 8. A prostaglandin analog according to claim 5, wherein M₁ is ##STR10##
 9. A prostaglandin analog according to claim 8, wherein Z₁ is aromatic.
 10. 3,7-inter-m-Phenylene-3-oxa-4,5,6-trinor-PGF₂, p-benzaldehyde semicarbazone ester, a prostaglandin analog according to claim
 9. 11. A prostaglandin analog according to claim 8, wherein Z₁ is aliphatic.
 12. A prostaglandin analog according to claim 11, wherein R₇ is ##STR11##
 13. 9-Deoxy-9-methylene-16-phenyl-17,18,19,20-tetranor-PGF₂, p-acetamidophenyl ester, a prostaglandin analog according to claim
 12. 14. A prostaglandin analog according to claim 11, wherein R₇ is ##STR12##
 15. 9-Deoxy-9-methylene-15-methyl-16-phenoxy-17,18,19,20-tetranor-PGF₂, p-benzaldehyde semicarbazone ester, a prostaglandin analog according to claim
 14. 16. A prostaglandin analog according to claim 11, wherein R₇ is --(CH₂)_(m) --CH₃ --.
 17. 9-Deoxy-9-methylene-16,16-dimethyl-PGF₂, p-benzaldehyde semicarbazone ester, a prostaglandin analog according to claim
 16. 